As I am moving deeper into my middle years I am coming to the conclusion that I am more gay than straight. Not that I don’t love sex with women. I do. There is still nothing more welcome to me than a warm wet vagina. But male-female relationships are too complicated. Trust me, I have plenty of older women eager to play with me, but the younger ones no longer find me appealing and I just don’t find an older woman sexually attractive. Most women want more than sex, while most men want just sex.
As I take inventory of my blessedly full sex life, I find myself now playing catch-up when it comes to homo-sex. With women when opportunity struck, I struck. But with men, I must sadly admit I let many chances for some great thrills go by either because at that time I was reluctant to let my homosexual side come out or I didn’t know what move to make, or I simply wasn’t aware of the possibilities.
Many of you have read my stories–they’re all true. There was the cowboy(s), Miss Karen and her hot male muse, and of course that lovely couple from Chicago who introduced me to cross dressing at the exotic clothing convention. There was my father and his uncut cock. To many of you I might seem to have had the best of both worlds, but I still carry around lots of coulda, shoulda, wouldas.
While I was engaged to my ex-wife I had moved in with a gay guy who wanted me sexually but I chose to remain aloof, despite having passed his bedroom one morning while he slept naked and noticing that he had a glorious big cock. Instead of going over to the bed, grabbing that schlong and putting it in my mouth, I walked on by. Damn that was a nice one.
This very same guy had a former lover/roommate who was a cute Latino boy, very effeminate with a perfect ass. He used to harass Jeff after he kicked him out—even come around uninvited—and he would always flirt with me. Out of respect for Jeff I shunned him. There were nights he would hang around outside our house begging to be let in. Since then I have learned he used to sit outside my window and watch me jerk off to transvestite porn. To think, I could have had his sweet butt and cute cock so many times. Crazy me.
After my divorce I roomed with a woman who had hired a Filipino houseman. Occasionally he would come and clean while I was at home and I would chat him up– and sort of flirt with him– but he showed no interest in me (since he spoke of a “she” in his life, I let any sexual thoughts go). The roommate and I worked together and I feared that the wrong reaction from Julio would have impacted things both at home and at work. Only after I had moved out my roommate told me that Julio was gay. Had I known that I certainly would have found the opportunity to seduce him somehow, some way.
Like most club members I love the occasional anonymous tryst. One night well after midnight while driving on the Interstate in Oregon, I pulled over at a rest stop. Wearing just a pair of gym shorts I headed into the men’s room. Soon after I closed the stall door I heard someone walk in and watched as they stood at the urinal an unusually long time. Eventually his feet disappeared. Soon I looked up and the guy was peering down at me over the partition, wet-eyed and smiling. I nervously flushed the toilet, pulled up my pants and left. What I should have done is show him my cock or…well, actually if then was now, I’d have been in that stall jerking off ready and hopeful that someone else would come in.
While married I walked on the wild side frequently. One time I hooked up with a beautiful blonde transvestite actress at a club in LA and took her home to her motel on Sunset Blvd. where we fucked and sucked. She was special because her cock was a mirror image of my own and I got to feel what my cock feels like to someone else (very interesting). This darling girl-boy said her girlfriend would be coming back from the same club sometime soon and would want to fuck, but since I had cum twice and was sexually spent I chose to leave. I later met that motel mate and he/she was equally as beautiful. Damn, I could have been sandwich by two beautiful trannies.
Speaking of trannies, in my Colorado days I worked in a building that was also a hotel. On this one particular Saturday I saw that they were hosting a Miss Gay Denver pageant in one of the ballrooms. I blew off my weekend office work, went home and leathered up.
My beautiful blonde hair and sculpted lean body turned many trannie heads that evening, especially this one beauty named Tommie from Boston. She asked me if I wanted to see her gown for the pageant and we went up to her room. I went straight for her sexy high heel pumps and stepped into them. I loved the feel of them on my naked feet and how they flattered my legs and ass.
Memories of dressing experiences came rolling back. I got incredibly aroused and showed her my erection. She came over and stroked it a bit while I stood in the high-heels. Then she started crying because she had to go downstairs for the contest but really preferred to play with me up there in her room. She promised me that after the show she and I could have the whole night. Instead, of course, I ended up sitting in the audience next to another lady boy who before the evening was over had gotten me off in the men’s room.
Another time in Minneapolis I decided to seek out a little stick-pussy and met a trans outside a huge gay club on Hennepin Ave. I invited her to go into the club with me. She demurred by saying, “But if you’ll take me to a place where I could buy some toot I’m yours for the rest of the night.” I passed on that invitation, thinking that it would be too much of a hassle and somewhat dangerous. Today? I’d have taken that hot trannie to Duluth if she had wanted.
In Chicago I was cruising the arcade floor of the Ritz Theater on Wells Street one night when I caught sight of this older gray-haired gentleman wearing sweat pants and no underwear, so his soft supple ass cheeks shook like a bowl of jelly. Our eyes eventually met and before long he ducked into a video booth that had a big glory hole.
I went in the adjacent stall and when he realized it was me next door, he forwent the usual hand and mouth preliminaries by immediately dropping the sweat pants and positioning his soft ass up to that hole. I quickly plunged my hot cock into what was a pre-lubed, very warm ass. And, oh my God, did he give me a great fuck. But rather than inviting him back to my hotel for more fun, which I definitely would have pursued today, I wiped off, zipped up and left. I still fantasize about what could have been that night.
There were also three different evenings during my married years when I was either swapping or doing threesomes with married couples. Each time the other guy had a really nice cock and I know he would have welcomed some favors from me, but I didn’t do it (couldn’t) for fear of being thought of as gay by my wife. Of course, that was the 1970s and 80s. Here in the century twenty-one I know I’d have diddled them.
In college I had several opportunities. One night when nineteen, I got drunk in a bar that turned out to be a gay drop late at night. I went with my boss whom later I learned was a gay. I got drunk but my friend Gary didn’t want to leave, so he arranged for a ride home for me and I was put into bed by a forty-ish friend of his who blurted out: “I could grab your dick, you know,” as he was taking off my pants.
I belligerently warned him not to. I should have let him because the next morning I woke up with a raging hard-on. That led me to a decision.
The next night I went over to my boss’s house and threw all caution to the wind. I eventually grabbed my boss’s dick…oh, and the next Friday night I actually let Gary’s friend grab my dick when at the bar, and the three off us ended up in a daisy chain on the floor in his house.